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| Halbfinale | | | | | |
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| Viertelfinale | | | | | |
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| Achtelfinale | | | | | |
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| 2.Runde | | | | | |
| 05.September 2023 | VfR Fehlheim | - | FC Bayern Alzenau | 1:4 |
| 19.September 2023, 19:30 Uhr | OSC Vellmar | - | Eintr. Stadtallendorf | |
| 19.September 2023, 19:30 Uhr | Türk Gücü Friedberg | - | | |
| 20.September 2023, 19:30 Uhr | Spvgg. Leusel | - | SV Steinbach | |
| 20.September 2023, 19:30 Uhr | Tuspo Mengeringhausen | - | FC Ederbergland | |
| 20.September 2023, 19:30 Uhr | Germ. Ober-Roden | - | RW Walldorf | |
| 20.September 2023, 19:30 Uhr | | - | FC Gießen | |
| 21.Oktober 2023, 15:00 Uhr | SG Ehrenberg | - | 1.FC Erlensee | |
| spielfrei: | FSV Frankfurt | | | |
| | Kickers Offenbach | | | |
| | KSV Hessen Kassel | | | |
| | SC Borussia Fulda | | | |
| | TSV Steinbach-Haiger | | | |
| | Fair-Play-Sieger | | | |
| | Fair-Play-Sieger | | | |
| | Fair-Play-Sieger | | | |
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| 1.Runde | | | - | | |
| 29.Juli 2023 | SG Ehrenberg | - | SG Bad Soden | 6:5 n.E. |
| 30.Juli 2023 | Tuspo Mengeringhausen | - | Lichtenauer FV | 1:0 |
| 30.Juli 2023 | VfR Fehlheim | - | RW Darmstadt | 3:2 |
| 30.Juli 2023 | SV Leusel | - | Melsunger FV | 3:1 |
| 30.Juli 2023 | SV Hummetroth | - | Germania Ober-Roden | 1:3 |
| 02.August 2023 | GW Bornheim | - | Türk Gücü Friedberg | 0:1 |
| 09.August 2023 | Viktoria Nidda | - | FC Erlensee | 0:3 |
| 09.August 2023 | TSV Zierenberg | - | OSC Vellmar | 0:4 |
| 09.August 2023 | FV Biebrich 02 | - | Rot-Weiss Walldorf | 0:4 |
| 09.August 2023 | TSV Bicken | - | Eintr. Stadtallendorf | 0:4 |
| 09.August 2023 | Niederaula/Kerspenhausen | - | SV Steinbach | 0:1 |
| 15.August 2023 | Spfr. Seligenstadt | - | Bayern Alzenau | 1:5 |
| 16.August 2023 | VfL Biedenkopf | - | FV Ederbergland | 0:2 |
| 16.August 2023 | FC Cleeberg | - | FC Gießen | 1:7 |
| 06.September 2023, 20:15 Uhr
| 1.FC Königstein | - | TuS Dietkirchen | |
| 06.September 2023, 19:30 Uhr | TGSV Holzhausen | - | FC Eddersheim | |
| spielfrei: | FSV Frankfurt | | | |
| | Kickers Offenbach | | | |
| | KSV Hessen Kassel II | | | |
| | SC Borussia Fulda | | | |
| | TSV Steinbach-Haiger | | | |
| | Fair-Play-Sieger | | | |
| | Fair-Play-Sieger | | | |
| | Fair-Play-Sieger | | | |
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